Hydrocarbon synthesis
View Patent ↗A method of synthesizing hydrocarbons from smaller hydrocarbons includes the steps of hydrocarbon halogenation, simultaneous oligomerization and hydrogen halide neutralization, and product recovery, with a metal-oxygen cataloreactant used to facilitate carbon-carbon coupling. Treatment with air or oxygen liberates halogen and regenerates the cataloreactant.
1. A method of making a product hydrocarbon having a carbon number C n , where n≧2, comprising:
reacting a halogenating agent with a reactant hydrocarbon having a carbon number C m , where m<n, to form a halogenated hydrocarbon;
contacting the halogenated hydrocarbon with a metal-oxygen cataloreactant to form hydrogen halide and a plurality of product hydrocarbons, wherein at least a portion of the product hydrocarbons have a carbon number C n , where n≧2, and wherein at least 50% of the product hydrocarbons are C 6 or higher hydrocarbons or at least 70% of the product hydrocarbons are C 5 or higher hydrocarbons;
trapping halogen from the hydrogen halide with the metal-oxygen cataloreactant;
recovering the product hydrocarbons; and
regenerating the metal-oxygen cataloreactant to recover the halogen.
2. The method of claim 1 , wherein at least 50% of the product hydrocarbons are C 6 or higher hydrocarbons.
3. The method of claim 1 , wherein at least 70% of the product hydrocarbons are C 5 or higher hydrocarbons.
4. The method of claim 1 , wherein at least 50% of the product hydrocarbons are C 6 or higher hydrocarbons and at least 70% of the product hydrocarbons are C 5 or higher hydrocarbons.
5. The method of claim 1 , wherein the reaction between the halogenating agent and the reactant hydrocarbon occurs at a reactant hydrocarbon-to-halogenating agent ratio of from 1:10 to 100:1 by volume.
6. The method of claim 1 , wherein the reaction between the halogenating agent and the reactant hydrocarbon occurs at a temperature of from 20° C. to 900° C. and a pressure of from 0.1 atm to 200 atm.
7. The method of claim 1 further comprising recycling the halogen as the halogenating agent to react with the reactant hydrocarbon.
8. The method of claim 1 further comprising allowing any C 1 to C 3 hydrocarbons, which are formed from allowing the halogenated hydrocarbon to contact the first metal-oxygen cataloreactant, to contact the first metal-oxygen cataloreactant again to form one or more C 4 or higher hydrocarbons.
9. A method of making a product hydrocarbon having a carbon number C n , where n≧2, comprising:
reacting a halogenating agent with a reactant hydrocarbon having a carbon number C m , where m<n, to form hydrogen halide and a halogenated hydrocarbon
contacting the halogenated hydrocarbon with a metal-oxygen cataloreactant to form a plurality of product hydrocarbons, wherein at least a portion of the product hydrocarbons have a carbon number C n , where n≧2, and wherein at least 50% of the product hydrocarbons are C 6 or higher hydrocarbons or at least 70% of the product hydrocarbons are C 5 or higher hydrocarbons;
trapping halogen from the hydrogen halide with the metal-oxygen cataloreactant;
recovering the product hydrocarbons; and
regenerating the metal-oxygen cataloreactant to recover the halogen.
10. The method of claim 9 , wherein at least 50% of the product hydrocarbons are C 6 or higher hydrocarbons.
11. The method of claim 9 , wherein at least 70% of the product hydrocarbons are C 5 or higher hydrocarbons.
12. The method of claim 9 , wherein at least 50% of the product hydrocarbons are C 6 or higher hydrocarbons and at least 70% of the product hydrocarbons are C 5 or higher hydrocarbons.
13. The method of claim 9 , wherein the reaction between the halogenating agent and the reactant hydrocarbon occurs at a reactant hydrocarbon-to-halogenating agent ratio of from 1:10 to 100:1 by volume.
14. The method of claim 9 , wherein the reaction between the halogenating agent and the reactant hydrocarbon occurs at a temperature of from 20° C. to 900° C. and a pressure of from 0.1 atm to 200 atm.
15. A method of making a product hydrocarbon having a carbon number C n , where n≧2, comprising:
reacting a halogenating agent with a reactant hydrocarbon having a carbon number C m , where m<n, to form a halogenated hydrocarbon;
contacting the halogenated hydrocarbon with a first metal-oxygen cataloreactant to form a hydrogen halide and a plurality of product hydrocarbons having a carbon number C n , where n≧2, at least 50% of which are C 6 or higher hydrocarbons or at least 70% of which are C 5 or higher hydrocarbons;
contacting the hydrogen halide with a second metal-oxygen cataloreactant to form a halogenated cataloreactant;
recovering the product hydrocarbons; and
contacting the halogenated cataloreactant with oxygen or air to regenerate the cataloreactant and form a molecular halogen.
16. The method of claim 15 , wherein at least 50% of the plurality of product hydrocarbons are C 6 or higher hydrocarbons.
17. The method of claim 15 , wherein at least 70% of the plurality of product hydrocarbons are C 5 or higher.
18. The method of claim 15 , wherein at least 50% of the plurality of product hydrocarbons are C 6 or higher and at least 70% of the plurality of product hydrocarbons are C 5 or higher.
19. The method of claim 15 further comprising: recycling the molecular halogen as the halogenating agent to react with the reactant hydrocarbon.
20. The method of claim 15 further comprising allowing any C 1 to C 3 hydrocarbons, which are formed from allowing the halogenated hydrocarbon to contact the first metal-oxygen cataloreactant, to contact the first metal-oxygen cataloreactant again to form one or more C 4 or higher hydrocarbons.